(S)-1-{(4R,5S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-methyl-4,5-dihydro-isoxazol-5-yl}-ethanol | 356068-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (S)-1-{(4R,5S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-methyl-4,5-dihydro-isoxazol-5-yl}-ethanol
• 英文别名: (1S)-1-[(4R,5S)-3-[(2R)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-4-methyl-4,5-dihydro-1,2-oxazol-5-yl]ethanol
• CAS: 356068-55-8
• 化学式: C₁₅H₃₁NO₃Si
• 分子量: 301.502
• InChiKey: XJDBYMHSPXXUPU-OPDFLTKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-{(4R,5S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-methyl-4,5-dihydro-isoxazol-5-yl}-ethanol 在 咪唑 、 samarium diiodide 、 ammonium heptamolybdate 、 水 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.08h， 生成 Benzoic acid (1R,2R,3R,7S)-7-{(4R,5S)-5-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methyl-4,5-dihydro-isoxazol-3-yl}-2-hydroxy-1,3-dimethyl-4-oxo-octyl ester
  参考文献：
  名称：

  Stereochemically Rich Pentaketides from Bis(isoxazolines):  A General Strategy for Efficient Polyketide Synthesis

  摘要：

  A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive opening of each isoxazoline sequentially or, alternatively, both simultaneously, potentially providing access to all stereoisomers of this carbon skeleton.

  DOI：

  10.1021/ol0490633
• 作为产物：
  描述：

  (S)-(-)-Z-3-penten-2-ol 、 (2R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methylpropanal oxime 在 次氯酸叔丁酯 、 乙基溴化镁 、 异丙醇 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-1-{(4R,5S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-methyl-4,5-dihydro-isoxazol-5-yl}-ethanol
  参考文献：
  名称：

  Stereochemically Rich Pentaketides from Bis(isoxazolines):  A General Strategy for Efficient Polyketide Synthesis

  摘要：

  A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive opening of each isoxazoline sequentially or, alternatively, both simultaneously, potentially providing access to all stereoisomers of this carbon skeleton.

  DOI：

  10.1021/ol0490633

文献信息

• A General Solution to the Modular Synthesis of Polyketide Building Blocks by Kanemasa Hydroxy-Directed Nitrile Oxide Cycloadditions
  作者：Jeffrey W. Bode、Nina Fraefel、Dieter Muri、Erick M. Carreira

  DOI：10.1002/1521-3773(20010601)40:11<2082::aid-anie2082>3.0.co;2-1

  日期：2001.6.1

  starting materials suffice for the modular synthesis of all possible polypropionate diastereomers. This general method for the diastereoselective synthesis of syn, anti, and methyl ketone aldol adducts utilizes a powerful MgII -mediated, hydroxy-directed nitrile oxide cycloaddition. The free hydroxy group provides an ideal synthetic handle enabling the rapid assembly of complex polyketide structures

  单一，便捷的反应方案和易于获得的同一套起始原料就足以用于所有可能的聚丙烯酸酯非对映异构体的模块合成。这种非对映选择性合成顺式，反式和甲基酮醛醇醛加合物的通用方法利用了功能强大的Mg II介导的，羟基定向的丁腈氧化物环加成反应。游离羟基提供了理想的合成手感，能够快速组装复杂的聚酮化合物结构。TBS = tBuMe 2 Si。